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Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d ‐Proline from Furfural
Author(s) -
Song Song,
Fung Kin Yuen Vincent,
Di Lu,
Sun Qiming,
Zhou Kang,
Yan Ning
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202006315
Subject(s) - furfural , chemistry , biorefinery , raw material , reductive amination , commodity chemicals , decarbonylation , yield (engineering) , pyrrole , catalysis , biomass (ecology) , organic chemistry , materials science , metallurgy , oceanography , geology
Production of renewable, high‐value N‐containing chemicals from lignocellulose will expand product diversity and increase the economic competitiveness of the biorefinery. Herein, we report a single‐step conversion of furfural to pyrrole in 75 % yield as a key N‐containing building block, achieved via tandem decarbonylation–amination reactions over tailor‐designed Pd@S‐1 and H‐beta zeolite catalytic system. Pyrrole was further transformed into dl ‐proline in two steps following carboxylation with CO 2 and hydrogenation over Rh/C catalyst. After treating with Escherichia coli, valuable d ‐proline was obtained in theoretically maximum yield (50 %) bearing 99 % ee. The report here establishes a route bridging commercial commodity feedstock from biomass with high‐value organonitrogen chemicals through pyrrole as a hub molecule.